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CA2373927A1 - Improved process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom - Google Patents

Improved process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom Download PDF

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Publication number
CA2373927A1
CA2373927A1 CA002373927A CA2373927A CA2373927A1 CA 2373927 A1 CA2373927 A1 CA 2373927A1 CA 002373927 A CA002373927 A CA 002373927A CA 2373927 A CA2373927 A CA 2373927A CA 2373927 A1 CA2373927 A1 CA 2373927A1
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CA
Canada
Prior art keywords
salts
preparation
improved process
derived therefrom
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002373927A
Other languages
French (fr)
Other versions
CA2373927C (en
Inventor
Rawle I. Hollingsworth
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Michigan State University MSU
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to CA002523096A priority Critical patent/CA2523096A1/en
Publication of CA2373927A1 publication Critical patent/CA2373927A1/en
Application granted granted Critical
Publication of CA2373927C publication Critical patent/CA2373927C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

An improved process for the preparation of 3,4-diyhdroxybutanoic acid (1) and salts thereof from a D- or L-hexose source is described. The process uses an alkali metal or alkaline earth metal hydroxide and peroxide oxidizing agent to convert the D- or L-hexose source to (1) by maintaining a low concentration of base and oxidizing agent in the reaction mixture at any one time and by maintaining a temperature between about 25 °C and 80 °C.
Upon acidification of the reaction mixture the 3-hydroxylactone is produced. The compound (1) is useful as a chemical intermediate to naturally occurring fatty acids and is used to prepare 3,4-dihydroxybutanoic acid-gamma-lactone (2) and furanone (3), particularly steroisomers of these compounds.
CA002373927A 2000-04-24 2001-03-05 Improved process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom Expired - Fee Related CA2373927C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002523096A CA2523096A1 (en) 2000-04-24 2001-03-05 Improved process for the preparation of 3,4-dihydroxybutanoic acid

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/556,532 2000-04-24
US09/556,532 US6239311B1 (en) 2000-04-24 2000-04-24 Process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom
PCT/US2001/006876 WO2001081289A1 (en) 2000-04-24 2001-03-05 Improved process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002523096A Division CA2523096A1 (en) 2000-04-24 2001-03-05 Improved process for the preparation of 3,4-dihydroxybutanoic acid

Publications (2)

Publication Number Publication Date
CA2373927A1 true CA2373927A1 (en) 2001-11-01
CA2373927C CA2373927C (en) 2007-05-29

Family

ID=24221740

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002373927A Expired - Fee Related CA2373927C (en) 2000-04-24 2001-03-05 Improved process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom

Country Status (7)

Country Link
US (1) US6239311B1 (en)
EP (1) EP1187800A4 (en)
JP (2) JP3817479B2 (en)
KR (1) KR100470005B1 (en)
AU (1) AU2001241962A1 (en)
CA (1) CA2373927C (en)
WO (1) WO2001081289A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102040856B1 (en) 2012-06-04 2019-11-05 제이엔씨 주식회사 METHOD FOR PRODUCING β-(METH)ACRYLOYLOXY-γ-BUTYROLACTONE

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4326072A (en) * 1980-07-01 1982-04-20 Ici Americas Inc. Ruthenium catalyzed hydrogenation of D-glucuronic acid
US4432801A (en) * 1981-05-04 1984-02-21 Grace Italiana S.P.A. Process for controlled degradation of liquid glucose syrups and cement additive products therefrom
CA2049536C (en) * 1991-05-13 1999-07-06 Rawle I. Hollingsworth Process for the preparation of 3,4-dihydroxybutanoic acid and salts thereof
KR100310935B1 (en) * 1998-07-24 2001-10-18 박영구 Continuous process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone

Also Published As

Publication number Publication date
JP2003531185A (en) 2003-10-21
CA2373927C (en) 2007-05-29
EP1187800A1 (en) 2002-03-20
KR100470005B1 (en) 2005-02-04
US6239311B1 (en) 2001-05-29
AU2001241962A1 (en) 2001-11-07
JP2005194282A (en) 2005-07-21
JP3817479B2 (en) 2006-09-06
KR20020019046A (en) 2002-03-09
EP1187800A4 (en) 2005-09-28
WO2001081289A1 (en) 2001-11-01

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Effective date: 20130305